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Prepare the Date Caramel Filling: Place the chopped dates in a heatproof bowl and pour the boiling water over them. Let them soak for 10 minutes to soften.

Drain the dates, reserving 1 tablespoon of the soaking liquid. Transfer the dates to a food processor along with the softened butter, light brown sugar, ground cinnamon, ground nutmeg, salt, and the reserved soaking liquid. Process until a smooth, thick paste forms. Scrape down the sides as needed. Set aside.

Prepare the Babka Dough: In a large bowl, whisk together 3 cups of the all-purpose flour, granulated sugar, active dry yeast, and salt.

In a separate bowl, whisk together the warmed milk, large eggs, egg yolk, and vanilla extract.

Pour the wet ingredients into the dry ingredients and mix with a wooden spoon or a stand mixer with a dough hook attachment on low speed until a shaggy dough forms, about 2 minutes.

Gradually add the softened butter pieces, one at a time, mixing until each piece is mostly incorporated before adding the next. The dough will be very sticky at this stage.

Increase the mixer speed to medium-low and knead for 8-10 minutes, or turn the dough out onto a lightly floured surface and knead by hand, adding the remaining 1/4 cup of flour as needed, until the dough is smooth, elastic, and no longer sticky. It should pass the 'windowpane test' (you can stretch a small piece thin enough to see light through it without tearing).

Lightly grease a large bowl. Place the dough in the bowl, turning to coat. Cover the bowl with plastic wrap and let it rise in a warm place for 1 1/2 to 2 hours, or until doubled in size. Alternatively, for a deeper flavor, refrigerate the dough overnight (8-12 hours) for its first rise.

Once the dough has risen, gently punch it down to release the air. Lightly flour a work surface and roll the dough into a large rectangle, approximately 12x18 inches.

Evenly spread the date caramel filling over the entire surface of the rolled-out dough, leaving a small border (about 1/2 inch) on one of the longer sides.

Starting from the longer side opposite the border, tightly roll the dough into a log. Pinch the seam to seal it.

Using a sharp knife, cut the log lengthwise down the middle, creating two halves with the swirled filling exposed.

Carefully twist the two halves together, keeping the cut sides facing up, to create a braided effect. Pinch the ends together to seal.

Lightly grease a 9x5-inch loaf pan. Carefully transfer the twisted dough into the prepared loaf pan. Cover loosely with plastic wrap or a clean kitchen towel and let it rise in a warm place for another 45-60 minutes, or until visibly puffy.

Preheat your oven to 350°F (175°C).

Bake the babka for 35-45 minutes, or until golden brown on top and a wooden skewer inserted into the center comes out clean. If the top browns too quickly, loosely tent it with aluminum foil.

While the babka is baking, prepare the Sugar Syrup: In a small saucepan, combine the granulated sugar and water. Bring to a simmer over medium heat, stirring until the sugar dissolves. Remove from heat and set aside.

Immediately upon removing the babka from the oven, brush the top generously with the prepared sugar syrup. Let the babka cool in the pan for 10-15 minutes before carefully transferring it to a wire rack to cool completely.


Prepare the Date Caramel Filling: Place the chopped dates in a heatproof bowl and pour the boiling water over them. Let them soak for 10 minutes to soften.

Drain the dates, reserving 1 tablespoon of the soaking liquid. Transfer the dates to a food processor along with the softened butter, light brown sugar, ground cinnamon, ground nutmeg, salt, and the reserved soaking liquid. Process until a smooth, thick paste forms. Scrape down the sides as needed. Set aside.

Prepare the Babka Dough: In a large bowl, whisk together 3 cups of the all-purpose flour, granulated sugar, active dry yeast, and salt.

In a separate bowl, whisk together the warmed milk, large eggs, egg yolk, and vanilla extract.

Pour the wet ingredients into the dry ingredients and mix with a wooden spoon or a stand mixer with a dough hook attachment on low speed until a shaggy dough forms, about 2 minutes.

Gradually add the softened butter pieces, one at a time, mixing until each piece is mostly incorporated before adding the next. The dough will be very sticky at this stage.

Increase the mixer speed to medium-low and knead for 8-10 minutes, or turn the dough out onto a lightly floured surface and knead by hand, adding the remaining 1/4 cup of flour as needed, until the dough is smooth, elastic, and no longer sticky. It should pass the 'windowpane test' (you can stretch a small piece thin enough to see light through it without tearing).

Lightly grease a large bowl. Place the dough in the bowl, turning to coat. Cover the bowl with plastic wrap and let it rise in a warm place for 1 1/2 to 2 hours, or until doubled in size. Alternatively, for a deeper flavor, refrigerate the dough overnight (8-12 hours) for its first rise.

Once the dough has risen, gently punch it down to release the air. Lightly flour a work surface and roll the dough into a large rectangle, approximately 12x18 inches.

Evenly spread the date caramel filling over the entire surface of the rolled-out dough, leaving a small border (about 1/2 inch) on one of the longer sides.

Starting from the longer side opposite the border, tightly roll the dough into a log. Pinch the seam to seal it.

Using a sharp knife, cut the log lengthwise down the middle, creating two halves with the swirled filling exposed.

Carefully twist the two halves together, keeping the cut sides facing up, to create a braided effect. Pinch the ends together to seal.

Lightly grease a 9x5-inch loaf pan. Carefully transfer the twisted dough into the prepared loaf pan. Cover loosely with plastic wrap or a clean kitchen towel and let it rise in a warm place for another 45-60 minutes, or until visibly puffy.

Preheat your oven to 350°F (175°C).

Bake the babka for 35-45 minutes, or until golden brown on top and a wooden skewer inserted into the center comes out clean. If the top browns too quickly, loosely tent it with aluminum foil.

While the babka is baking, prepare the Sugar Syrup: In a small saucepan, combine the granulated sugar and water. Bring to a simmer over medium heat, stirring until the sugar dissolves. Remove from heat and set aside.

Immediately upon removing the babka from the oven, brush the top generously with the prepared sugar syrup. Let the babka cool in the pan for 10-15 minutes before carefully transferring it to a wire rack to cool completely.
